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Check Cherry ★ 5.0 · 23 reviews
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Check Cherry

Event booking software where clients book easily, submit details through their portal, and your team stays coordinated.

AiDOOS Verified SAAS Marketing
5.0 ★★★★★ 23 reviews
Live in 72 hours 14-day free trial
Starting from
$39
per user / month
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14-day free trial · No credit card required

Category
Marketing
Deployment
Cloud (SaaS)
API Access
Yes
AiDOOS Deploy
72 hours

About Check Cherry

Check Cherry is an all-in-one booking and business management platform designed specifically for event professionals such as DJs, photo booth operators, photographers, and mobile bartenders. It streamlines the entire client journey: online booking, proposals, contracts with e-signatures, payment processing, client portals, and automated follow-ups. The platform also includes staff scheduling, a mobile app for iOS and Android, and an AI assistant integration via MCP for business insights. Trusted by thousands of event pros, Check Cherry has processed over $251 million in bookings and handled more than 246,000 events. AiDOOS enhances deployment and adoption by providing a dedicated customer success team that assists with setup, migration from existing tools, and ongoing support, ensuring a seamless transition and maximizing the platform's value. With a 14-day free trial and plans starting at $39 per month, Check Cherry aims to reduce friction for both the business and its clients, leading to smoother events and happier customers.

Challenges It Solves

  • Managing bookings and client communication across scattered tools like spreadsheets and email.
  • Chasing payments and contracts manually, causing delays and friction.
  • Struggling with client no-shows and missed details due to lack of centralized information.
  • Difficulty scaling event business without increasing administrative overhead.

Screenshots

Check Cherry screenshot 1
Check Cherry screenshot 1 Check Cherry screenshot 2 Check Cherry screenshot 3 Check Cherry screenshot 4 Check Cherry screenshot 5 Check Cherry screenshot 6

Use Cases

For DJs

Manage song lists, timelines, and contracts while accepting bookings and payments online.

For Photo Booth Operators

Handle backdrops, templates, and add-ons with a client portal that simplifies event details.

For Mobile Bartenders

Set travel fees and service add-ons, and automate contracts and payments for events.

Pricing

Standard
Best for new businesses and part-timers. Includes 30 upcoming bookings, 2 admin accounts, 2 brands, unlimited staff and client accounts, and all core features.
$39/user
billed monthly ·
  • Online booking
  • Proposals
  • Contracts
  • Payments
  • Client portal
  • Mobile apps
  • Automations
Unlimited
Best for high-volume businesses and staff. Includes unlimited upcoming bookings, 10 admin accounts, 6 brands, and all features.
Custom
contact AiDOOS for pricing
  • Everything in Growth
  • Unlimited bookings
  • More admin accounts and brands
14-day free trial available — No credit card required. Full access to all features.
💡 Pricing insight from reviewers: Check Cherry is competitively priced at $39/month for the Standard plan, with annual billing offering two months free.

Key Features

Online Booking

Clients can book your services directly through your website or booking link.

Proposals & Contracts

Create professional proposals and contracts with e-signatures to close deals faster.

Payment Processing

Accept credit cards, Apple Pay, and bank transfers with automatic invoicing and payment plans.

Client Portal

Clients have a dedicated portal to view bookings, pay invoices, and submit event details.

Staff Scheduling

Assign staff to events, manage availability, and send reminders.

Automated Messaging

Automate email and SMS follow-ups, payment reminders, and client communications.

What Reviewers Say AI-synthesized from 23 reviews

What works well

  • Ease of use and intuitive interface praised by users.
  • Time-saving features that streamline booking and client management.
  • Fast customer support with typical response time of 2-5 minutes.

Common concerns

  • No self-service import tool for existing clients; requires manual import with team assistance.
  • Limited to English and certain countries.

Reviews

23 verified reviews
5.0
★★★★★
out of 5 · 23 reviews
O
Owner
"Easily Streamlined Our Photo Booth Business"
I appreciate Check Cherry's ease of use for both me and my clients. The client portals are exceptional and include everything I need. These portals significantly cut down on back-and-forth communication because clients can book and modify their reservations themselves. Initial setup was incredibly simple, aided by their videos, training materials, and rapid customer support responses. N/A I rely on Check Cherry to manage my photo booth business, handling clients and keeping me organized. It's easy for all users, with outstanding client portals that reduce communication by enabling self-service bookings and changes.
F
Founder
"Check Cherry: Efficient Booking Hub with Great Automation"
I love having an overview of every booking detail. It has solid auto functions yet allows manual customization for my operations. It keeps my team organized and alerts them about event bookings, which I love. It also helps me track whether we've booked clients, avoiding under- or over-charging. Team members' calendars sync with booking gigs, and they receive text notifications about their assigned events—one less task for me. They get automated texts for pre-event forms, post-event forms, or manuals, making access easy. More visual pipeline views per event would be nice. Check Cherry keeps us organized and professional. It automates notifications, saves time, and lets me review bookings for pricing. My team stays informed with automatic alerts, streamlining operations.
O
Owner
"Top-Notch Customer Service and Time-Saving Automations"
Without question, the customer service stands out! I also appreciate how it reduces time through automations and minimizes repetitive tasks. Whenever something isn't working correctly or needs an update, their team is approachable. I genuinely can't think of any dislikes. If I have an issue, I discuss it with them, and either they release a new feature or offer a workaround based on my needs and current capabilities. Automation and repetition save time, allowing me to focus elsewhere. The software is easy to use, so integrating all its features is straightforward.
O
Owner
"A Lifesaver for Event Rentals with Exceptional Support"
Running an event rental business, I rely on Check Cherry for bookings, and it's been a fantastic addition. Booking and event management become effortless. Customers can book independently, and event planners can share referral links to earn commissions. This software simplifies life, and I recommend it fully. It's far more user-friendly than alternatives, and their support team is responsive and collaborative, answering messages quickly. If many users request a feature, they implement it. It handles all my booking, client management, and point-of-sale needs. I value its simplicity and ease of management. Automations are valuable because clients can book and manage without my involvement, saving substantial time. Initial setup was fast and easy, ensuring a smooth transition. Adding a security deposit feature would be nice. Check Cherry covers booking, client management, and point-of-sale. It's user-friendly, enables client self-service, saves time, simplifies event management, and supports referral commissions.
O
Owner
"Automation Streamlines Our Photo Booth Business"
I adore Check Cherry's automation capabilities because they let us respond to clients even while we're asleep. The ease of following up with customers and creating custom automations from scratch is my favorite feature. It's extremely helpful for organizing all client data, and the provided email templates are practical. Sending proposals is simple, and the proposal interface looks far better than my previous solution. Whenever I encounter an issue, support resolves it quickly. I use Check Cherry to manage client information, respond swiftly with templates and automations, and send proposals effortlessly with an improved interface.
F
Founder | EventLocker
"Check Cherry Simplified Our Booking Process and Saves Hours Weekly"
Check Cherry consolidates our entire booking and client management process into one dashboard, greatly improving operational efficiency. Creating custom packages, automating quotes, contracts, and payments, and managing events through an intuitive interface saves us many hours weekly. The system is user-friendly and quick to adopt, so we launched without intensive training. We also value the ability to tailor workflows for various event types (weddings, corporate, private), which boosts conversion rates and enhances the client experience. However, Check Cherry does have limitations in advanced customization and white-labeling, especially for multi-brand or partner setups. Pricing rules can be restrictive when handling different margins between our charges and those of partners. Deep automation features like conditional workflows, advanced upsells, or fine-grained integrations require workarounds. The mobile app is handy but could improve; editing emails on it is cumbersome—selecting text causes auto-scrolling within the small window, which may be an iPhone-specific issue. Check Cherry addresses the fragmentation between lead intake, quoting, contracting, and payments by uniting them. Before, we juggled multiple tools and manual coordination, leading to delays and missed bookings. Now we respond faster with professional automated quotes and booking flows, improving our conversion rate and response time. It also standardizes our process, offering a consistent, premium experience from first inquiry to event execution. Operationally, it reduces administrative work, freeing us to focus on sales, relationships, and delivering great events. This efficiency drives higher booking volume and easier scalability.
O
Owner
"Friendly, Easy-to-Use, and Continuously Enhanced with Responsive Founders"
What I appreciate most is the personal touch. We can directly speak with owners Judd and Matt to refine our usage. They're enthusiastic to assist and always welcome feedback for system improvements. We always feel valued and understood. We also love how straightforward it is for both us and our clients. Booking and customizing to our offerings is effortless. We've encountered no major issues, and whenever we need help, we get quick solutions. It effectively manages our bookings, displays availability, and showcases our services, making business operations smoother and letting us focus on what we enjoy most—attending events.
S
Small-Business (50 or fewer emp.)
"Unified Proposals, E-Signatures, and Payments—Perfect for Entertainment Companies"
Our clients now receive a single link instead of exchanging multiple emails and documents. They can view the proposal, select add-ons, sign, pay, and get automatic confirmations, receipts, and reminders. This streamlined experience looks professional and has cut down significantly on our team's administrative load. What sets Check Cherry apart is its tailored fit for entertainment businesses. It feels built specifically for companies like ours rather than forcing generic CRM to adapt. The only drawback is a slight learning curve during setup, but onboarding and support from Matt and Judd eased the process. Finding booking software designed for entertainment is rare; most options are either too broad or require workarounds for basic event bookings. Check Cherry has met our expectations perfectly. The platform has transformed our proposal and booking workflow. We can craft custom event packages, let clients choose optional extras, and send everything via one simple booking link. Clients appreciate the ease—they can review, sign, pick a payment method, and finish their booking in one spot. Automated receipts, reminders, and follow-ups have also minimized manual efforts.
O
Owner
"CheckCherry: An All-in-One CRM That Saves Time with AI Automation and Outstanding Support"
The most valuable aspect of CheckCherry is the time it saves me while keeping my operations organized. All necessary tools are consolidated—lead tracking, agreements, invoicing, payment handling, automated emails and texts, scheduling, and customer communication. I also appreciate that the platform is continuously evolving. The team regularly introduces new capabilities, especially the recent AI features, demonstrating their dedication to staying current. In addition, their customer support is unparalleled. Whenever I've sought assistance, I've received quick, knowledgeable, and friendly help. The standout feature is CheckCherry's high customizability paired with user-friendliness. I've explored other CRMs, and none have combined simplicity, flexibility, and powerful automation like CheckCherry. I don't use their music collection forms because other software suits my needs better. CheckCherry has addressed a major challenge of running an event business: staying organized while delivering rapid, professional client communication. Previously, I spent excessive time manually chasing leads, sending contracts and invoices, tracking payments, and recalling each client's booking stage. Now these processes are automated, freeing up hours weekly and preventing oversights. The automated email and texting alone have boosted my response speed and client experience, and integrated payments simplify online booking and payment for clients. Customization has allowed me to design workflows that match my business rather than adapting my operations to the software. In summary, CheckCherry has made my business more efficient, professional, and scalable. I devote less time to admin and more to serving clients and growing the company.
O
Owner
"Highly Dependable Platform with Rapid, Considerate Assistance"
The platform itself is excellently constructed and obviously designed with dependability as a top priority. Still, the main factor that keeps me returning each year is their support. Judd and Matt consistently enhance the service and respond to any inquiries at incredible speed. They also carefully analyze how end users will actually work with the system and then introduce ideas we'd never have come up with ourselves. I wholeheartedly endorse Check Cherry, and I already recommend it to numerous people in our field. It would be great if the entry-level plan allowed more bookings, and having additional custom status options to quickly identify pending items for clients would be beneficial, but Judd and Matt constantly improve other areas. The tool helps us monitor customers, their needs, and our interactions.

Reviewer Demographics

Top Industries

No data available

Enterprise Readiness

PCI DSS

Identity & Access

SSO✗ Not supported
RBAC Role-based access with admin, staff, and client levels.
Audit Logs

Data Security

At restAES-256
In transitTLS 1.2+
Key mgmtVendor-managed

SLA & Availability

Uptime SLA99.9%
RPO
RTO
Pen test

Compliance & Portability

Data residency
Data export
Right to erasure

Integrations

AI Assistant (MCP)

Connect Check Cherry to AI assistants like ChatGPT and Claude via MCP to ask questions about bookings, leads, and payments.

Native ~2 minutes ⇄ Bi-directional

Canva

Connect Canva account to import designs directly into Check Cherry media library.

Third_Party < 1 hour

Stripe

Integration allows connecting an existing Stripe account for payment processing.

Third_Party 1-2 hours ⇄ Bi-directional

Google Calendar

Sync Check Cherry calendar with Google Calendar to manage availability and bookings.

Third_Party < 1 hour ⇄ Bi-directional

QuickBooks

Integration to sync accounting data between Check Cherry and QuickBooks.

Third_Party 1-2 hours ⇄ Bi-directional

Twilio

Integration that enables sending and receiving SMS messages through Check Cherry.

Third_Party 1-2 hours ⇄ Bi-directional

Zapier

Connect Check Cherry to thousands of other apps via Zapier automations.

Third_Party 1-2 hours ⇄ Bi-directional

WordPress

Embed Check Cherry booking links and forms on WordPress websites.

Third_Party < 1 hour

Governance & Compliance

EU AI Act

No data available

Data Processing Agreement

No data available

Sub-processors

No data available

Right to Erasure

No data available

Change Notifications

No data available

NIST AI RMF

No data available

AiDOOS Managed Deployment

Deploy Check Cherry in 72 hours

AiDOOS handles setup, CRM integration, SSO config, and user provisioning. Your team goes live — not your IT department.

12
Deployments
94%
Adoption rate
4.8/5
Post-deploy sat.
1-2 weeks
Time to value

Prerequisites

  • Active Check Cherry subscription
  • Admin access to Check Cherry account
  • Payment processor configured

Configuration Options

  • Configure staff roles
  • Set up payment plans
  • Customize client portal
  • Integrate with external calendar

How Check Cherry Compares

Product AI & Analytics Ease of Use Enterprise Features Pricing Integrations Mobile Experience Quick Setup Customer Support Rating Price/mo
Check Cherry This product
Good Excellent Fair Excellent Fair Excellent Excellent Excellent ★ 5.0 $39/user
HoneyBook
Fair Good Good Fair Good Good Good Good $32/user
Dubsado
Poor Fair Fair Excellent Fair Fair Fair Fair $20/user
Booqable
Fair Good Good Good Good Good Good Good $39/user
Virtual Delivery Center · A new delivery category

A Virtual Delivery Center for Check Cherry

Pre-vetted experts and AI agents in the loop, assembled as a delivery pod. Pay in Delivery Units — universal pricing across roles, seniority, and tech stacks. No hiring, no contracting, no procurement cycle.

  • Plans from $2,000 — Starter Pack, 10 Delivery Units, 90 days
  • Refundable on unused Delivery Units, anytime — no questions asked
  • Re-delivery guarantee on acceptance miss
  • Pre-flight delivery sizing — you see the plan before you commit

How a Virtual Delivery Center delivers Check Cherry

Outcome-based delivery via AiDOOS’s VDC model.  Why VDC vs traditional consulting? →

Outcome-Based

Pay for results, not hours

Milestone-Driven

Clear deliverables at each phase

Expert Network

Access to certified specialists

Implementation Timeline

1
Discover
Requirements & assessment
2
Integrate
Setup & data migration
3
Validate
Testing & security audit
4
Rollout
Deployment & training
5
Optimize
Performance tuning
Schedule a Meeting

Frequently Asked Questions

How long does it take to get set up?
Most users are set up in under an hour, but AiDOOS can handle deployment and configuration for you in 72 hours with full integration support.
Does Check Cherry have a mobile app?
Yes, Check Cherry offers native iOS and Android apps that allow you to manage bookings, payments, and client communication on the go.
Can I integrate Check Cherry with my existing website?
Absolutely. Check Cherry can be integrated with WordPress, Squarespace, Wix, and custom websites by embedding booking links and forms.
What payment methods does Check Cherry support?
Check Cherry supports credit cards, debit cards, Apple Pay, Google Pay, and bank transfers through its built-in payment processing.
Does Check Cherry offer a free trial?
Yes, Check Cherry offers a 14-day free trial with full access to all features. No credit card is required to start the trial.
Can I automate payments and reminders?
Yes, Check Cherry allows you to set up automatic payment schedules and send automated reminders to clients, reducing manual follow-ups.

Quick Stats

★ 5.0
Rating
12
Deployments
72 hours
Live in
99.9%
Uptime SLA
Deployment Complexity
Easy (2/5)
Schedule a Meeting

Vendor

Check Cherry
Founded 2016 · Redlands, US
Verified Vendor

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